39th Annual Loudoun Street Mile 2026

The Loudoun Street Mile is a straight one-mile course along Loudoun Street in Historic Old Town Winchester, Virginia, ending in the Old Town Mall. It takes place in late May near Memorial Day. A non-competitive fitness walk precedes the mile heats, and a Tot Trot for children follows the final wave. The main mile is open to participants aged 6 to 105. Race-day registration is unavailable as the field is arranged into timed waves. The fastest men begin the race, followed by the fastest women. Subsequent waves are ordered by entry time, with starts approximately 10 minutes apart. The event attracts competitive runners as it functions as an RRCA state championship and a Collegiate Running Association road mile championship. Prize money is awarded to the top overall finishers, masters runners, and CRA collegians. Age-group awards extend to young children and older participants, making the short downtown course suitable for elite racers, club runners, families, walkers, and newcomers.